Calculate the odds of success, and you may get some sats...

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Is it 1/20?

Unless there is an interaction between the dice I'm not seeing without thinking too hard... ~4.3%. 23 possible values rolled with 22 of them being a fail. 1 in 23 chance of success, 1/23 is .0435 after rounding. I think that is close enough for our purpose here.

On the right track but not it.

There are two dice rolls. A d20 and a d4.

Ah, so the dice do interact I probably should have seen that. In that case, you must roll a 1 in 20 and and a 1 in 4. 1/20 is .05, 1/4 is .25. .05*.25=.0125 or 1.25% chance of success.

Making progress but need to account for the charisma modifier, and the challenge (22 or higher for success)

I did, you need perfect rolls on both die to win. 24 (-1 one for the modifier makes 23) is the only possible role higher than the challenge value. Unless you win the challenge on a tie, I never played much DND and don't remember. If you win on a tie, what a mess to calculate.

you win on a tie

So 2 in 20 * 1 in 4 + 1 in 20 * 2 in 4, those include the perfect roll but you must respect order of operations.

All that math to arrive at a round 5%.

I'm reminded of those questions the teachers gave to fuck with you in higher math. "there is no way the answer to a college calculus problem is 7, I must have made a mistake"

Would you believe this is still incorrect

I might, I only took stats 1 and that was many years ago.

its interesting to see how you're thinking through the problem though

Doing the wrong math or doing the math wrong?

I know I'm close enough to make the informed decision I don't like those odds.

Go back to this. Its close, but not quite how the odds are statistically calculated

So 2 in 20 * 1 in 4 +

..... 1 in 20 * 2 in 4, ....